What I Wish I Knew After Selling
A personal reflection on letting go, moving on, and the emotional side of exits.
When we sold our family business, we had a plan. We agreed to stay on for up to five years and help grow the company under its new ownership. We believed in the buyer, saw alignment in strategy, and were excited to help lead the expansion in North America.
For a while, it felt like the right decision. But slowly, things changed. Their strategy shifted, our influence narrowed, and the writing was on the wall by the end of our first year. My parents left after 18 months. I stayed until month 23.
I don’t regret the deal, and I’d do it again. We sold for all the right reasons and got exceptional value for the company. But that doesn’t mean the transition wasn’t hard.
The Misalignment You Don’t See Coming
The truth is, once you sell, it’s their company. No matter what the transition plan says. No matter how aligned you feel on Day One.
I remember a meeting where we presented what we felt was a strong case and a well-prepared plan to follow through on the strategy we thought we had agreed to execute. We were ready for discussion, even disagreement. But what we got was a flat “no.” There was no debate, no alternative plan, just a signal that the direction had changed — and that we weren’t part of it.
That moment was clarifying. And deeply frustrating. I wish I had accepted the reality sooner: the new owners didn’t value our contribution as we hoped. And once you’re no longer the owner, that’s their right.
What I Wish I Realized Sooner
Looking back, I don’t regret the sale. But I wish I had recognized what should have been clear: that the new ownership no longer valued my contribution in the same way.
At some point, your own company, through new owners, new executives, or simply new priorities, may stop seeing you as essential. That’s not personal. But it can feel like a loss. I spent too long trying to fit into a role that no longer existed, and in hindsight, I wish I’d allowed myself to accept that earlier.
I wish I had understood sooner that once you sell, your business is no longer yours, not in the way it once was. It’s easy to get caught in the continuity mindset, believing that your role, perspective, and influence will carry the same weight. But it’s not the same company. Even if the work looks familiar and the people are the same, the center of gravity has shifted.
One of the hardest parts of the transition is truly accepting that change. I spent too long resisting it, trying to stay connected to a version of the company that no longer existed. Letting go isn’t about defeat. It’s about recognizing that your chapter has ended, even if the business continues.
The In-Between Is Real
I left the company in November 2018. And for a while, I did almost nothing. Not because I didn’t want to work, but because I was exhausted.
This wasn’t just a business I had run for years — it had been part of my life for as long as I could remember. When I left, I wasn’t just walking away from a role. I was walking away from a part of my identity.
There was no big a-ha moment, no brilliant idea, just space, and eventually, clarity. I started having conversations with friends and colleagues about buying, selling, and transitioning businesses. I talked about what worked, what didn’t, what I wish I’d known, and what I saw in others.
At some point, someone said, “Could you help me with this?”
That was the start of Peninsula Road: a boutique advisory firm that helps owners prepare for sale, navigate transition, and move forward with clarity.
Why I Do This Work Now
While at our business, we made several acquisitions, many of them with sellers who didn’t have an advisor. Those deals were harder, not because the sellers weren’t smart or capable, but because they didn’t know what questions to ask, how the process should unfold, or who they could trust to help them find clarity when things got tough.
I try to bring that to my clients now: real-world insight from someone who’s lived it, someone who understands both the structure of the deal and its emotional weight.
Sellers carry a quiet burden. They worry about their teams, their legacy, and the next chapter. They feel a responsibility to everyone around them, and that’s entirely natural. But it’s worth remembering: you’ve already done more than most people realize.
You’ve held up your end of the bargain.
You made payroll. You took the risk of failure every day. You provided for families and created a place people were proud to work. That’s what matters. And you shouldn’t feel guilty for wanting a future that works for you, too.
Some owners stay on post-sale, and that can work — but only if they feel respected, fairly compensated, and aligned with the company’s direction. If those things fall apart, don’t stay out of habit or guilt. Leaving isn’t quitting. Sometimes it’s the most honest choice you can make.
And if you’re unsure what comes next, that’s okay too. You don’t need to have the next chapter written on Day One. Most people don’t. But giving yourself the time and space to find clarity is part of the process.
Even if you plan to stay on, it’s worth thinking ahead.
When we sold, I didn’t consider life after the business much. We intended to stay, and I assumed there’d be time to figure it out. But when things shifted faster than expected, it felt jarring. I wasn’t prepared because I hadn’t even considered that I might need to be.
That’s one of the reasons I do this work. Sellers don’t need someone to tell them how to feel; they need someone who’s been there, someone who can help them plan not just for the deal but also for the possibility that the path ahead may change.
If you’re starting to think about your exit, even loosely, this is the time to begin building your perspective. You don’t need a timeline; you just need to start talking about it.
Hope for the best. But plan for the rest.
That’s where advice from Peninsula Road can make the biggest difference.
A Final Thought
If someone asked me how it feels to sell something your family built, and then walk away from it, I’d say this:
It feels bittersweet. Both a feeling of achievement and a feeling of loss at the same time.
And that’s okay.
Ready to talk?
Whether you’re just starting to think about your next chapter or you’re further down the road, I’d be glad to have a real, no-pressure conversation about what comes next.